Planning a trip to the Windy City?
Chicago is undeniably one of the greatest cities in the world, but it can be incredibly overwhelming for first-time visitors.
Between the massive skyline, the sprawling neighborhoods, and the fiercely debated food scene, it is very easy to fall into the usual tourist traps.
We see it happen every single summer.
Visitors waste their vacation budget on overpriced attractions, sit in miserable traffic, and eat at the wrong restaurants.
But your Chicago vacation doesn’t have to be a stressful, expensive cliché.
Whether you are visiting Chicago for a quick weekend getaway or a week-long adventure, knowing what not to do is just as important as knowing what to see.
We want you to experience the real city like a local.
From the ultimate hot dog sin to the biggest transportation blunders, we’ve put together the ultimate cheat sheet for your trip.
Here are the 10 biggest rookie mistakes everyone makes when visiting Chicago—and exactly what you should do instead.
1. Staying Exclusively in the Loop
When booking a trip, most tourists immediately look for a hotel right in the middle of “The Loop” near Millennium Park.
While it makes sense on paper, The Loop is primarily a business and financial district.
When the office workers go home at 5:00 PM, the area completely empties out.
The restaurants close early, the streets get incredibly quiet, and you are left completely cut off from Chicago’s legendary nightlife.
What To Do Instead:
Chicago is a city of neighborhoods. If you want to experience the best food, bars, and culture, you need to sleep where the locals actually live.
Book a hotel in a vibrant neighborhood just outside the downtown core. You will get a much more authentic, exciting Chicago experience (and usually a better rate!).
Check out our article on the 9 best Chicago neighborhoods to explore
Where to stay instead:
For Foodies: Book the trendy Hoxton Hotel in the West Loop to be steps away from the city’s best restaurants
For Nightlife & Shopping: Stay at The Robey in Wicker Park for an incredibly cool, hipster-chic vibe.
For Classic Charm: Book the Hotel Lincoln in Lincoln Park to be right next to the zoo and the lakefront.
2. Overlooking Chicago’s Free & Cheap Attractions
A trip to a major city like Chicago can get expensive quickly.
Many first-time visitors get so focused on the big-ticket items—the museums, the observation decks, and the architectural boat tours—that their vacation budget evaporates in a matter of days.
They completely miss the fact that some of Chicago’s most iconic experiences cost absolutely nothing.
What To Do Instead:
Balance your itinerary with the city’s incredible free attractions.
You can spend an entire afternoon walking through the world-class Lincoln Park Zoo, which is one of the only free major zoos left in the entire country.
Next to the zoo is the stunning Lincoln Park Conservatory and the hidden Alfred Caldwell Lily Pool, both of which are also completely free to enter.
In the summer, skip the crowded hotel pools and head to North Avenue Beach or Oak Street Beach to relax on the sand and take in the unbelievable skyline views for free.
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3. Skipping the Architecture Boat Tour
After reading about tourist traps like Navy Pier, many visitors try to avoid all of the “touristy” activities on the water.
They see the boats full of people on the Chicago River and assume it’s just an overpriced, generic sightseeing cruise.
This is a massive mistake. Skipping the boat tour means missing out on what is arguably the single best experience in the entire city.
What To Do Instead:
Book a ticket for the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady.
This isn’t a cheesy tour with a pre-recorded narrator. This is a 90-minute masterclass in architectural history, led by some of the most passionate and knowledgeable docents you will ever meet.
You get to see the city’s most iconic skyscrapers from a completely unique perspective on the water while learning the wild, fascinating stories behind their construction.
Even the most cynical, born-and-raised Chicagoans will tell you that the architecture boat tour is 100% worth the money and the hype. It is the one “tourist” thing that everyone absolutely must do.
4. Not Asking Locals For Recommendations
Chicago is a massive city, and it can be intimidating.
Many visitors stick to what their phone tells them—relying on Google Maps and the top-rated spots on Yelp.
They see busy locals rushing to work and assume everyone is too busy or too unfriendly to help.
As a result, they miss out on the incredible, hidden neighborhood gems that are just one block off the main tourist path.
What To Do Instead:
Just ask!
Don’t let the big-city hustle fool you. Chicagoans are incredibly proud of their city, and most are more than happy to share their favorite spots.
Strike up a conversation with your bartender, your barista, or the person working at the front desk of your hotel.
Ask them for their favorite neighborhood Italian joint, the best dive bar for a cheap beer, or the most efficient way to get to the museum.
You’ll be rewarded with an authentic, off-the-beaten-path recommendation that you will never find on a generic travel blog.
5. Calling it the “Willis” Tower
In 2009, a London-based insurance broker bought the naming rights to Chicago’s tallest building and officially changed its name to the Willis Tower.
If you use that name out loud while walking down the street, every local within a 50-foot radius will instantly know you are a tourist.
What To Do Instead:
To a true Chicagoan, it will always be the Sears Tower. Even though the name technically changed over a decade ago, locals fiercely refuse to acknowledge it.
Do yourself a favor and just call it the Sears Tower. You will instantly earn the quiet respect of every local in the room.
6. Only Eating Deep Dish Pizza
Thanks to movies and travel shows, the rest of the world thinks Chicagoans sit around eating massive, three-inch-thick slices of deep dish pizza every single day.
We absolutely do not.
Deep dish is delicious, but it is incredibly heavy. Locals usually only eat it once or twice a year when out-of-town guests are visiting.
What To Do Instead:
If you want to eat pizza like an actual Chicagoan, you need to order “Tavern Style” also commonly called “Thin Crust”
This is the true staple of the Chicago diet. It features a cracker-thin crust, a sweet and tangy tomato sauce, and is almost always cut into tiny squares instead of traditional slices.
Head to a neighborhood spot like Vito & Nick’s or Pat’s Pizza, order a tavern-style pie, and wash it down with a cold pitcher of Old Style beer.
Check out our article on the must try foods in Chicago
7. Taking an Uber from O’Hare at Rush Hour
You just got off a long flight, you have your bags, and you naturally open your phone to call an Uber or a Lyft to your downtown hotel.
If you do this between 3:00 PM and 6:30 PM on a weekday, you are making a massive mistake.
The Kennedy Expressway (I-90) is notorious for having some of the worst, most soul-crushing rush hour traffic in the entire country.
A 15-mile ride that should take 30 minutes can easily trap you in the back of a cab for nearly two hours.
What To Do Instead:
Follow the signs in the airport for “Trains to City” and get on the CTA Blue Line.
The train drops you off right in the heart of downtown Chicago for just $5.
It completely bypasses all the highway traffic, saving you an incredible amount of time, money, and sanity right at the start of your trip.
Just be careful when riding the blue line at certain times.
8. Putting Ketchup on a Hot Dog
You step up to a classic Chicago hot dog stand, order your food, and casually ask the cashier for a packet of ketchup.
Do not do this.
In Chicago, putting ketchup on a hot dog is considered a culinary crime.
Many classic, old-school hot dog stands flat-out refuse to even keep ketchup in the building, and the staff will publicly shame you if you ask for it.
What To Do Instead:
Order it “dragged through the garden.”
A true Chicago-style hot dog is a masterpiece of flavor balance.
It features an all-beef frankfurter topped with yellow mustard, neon-green sweet relish, chopped white onions, tomato slices, a pickle spear, sport peppers, and a dash of celery salt—all on a poppy seed bun.
The tomatoes provide all the sweetness and acidity you need. You won’t even miss the ketchup.
9. Paying for the Skydeck But Not Visiting a Rooftop Bar
Millions of tourists flock to the top of the Sears Tower (aka the Willis Tower) to stand on “The Ledge”—the iconic glass box that juts out 1,353 feet above the city.
It’s an incredible, heart-stopping photo op, and it’s one of those “I was here” moments that many visitors want.
The mistake isn’t going to the Skydeck; it’s thinking that is the only great view in Chicago.
What To Do Instead:
The Skydeck gives you a jaw-dropping aerial view from the west, but a rooftop bar gives you the atmosphere of the city.
Instead of standing in a line, you can be sipping a world-class cocktail, listening to music, and watching the city lights glitter from an entirely different angle.
Head to Cindy’s Rooftop overlooking Millennium Park, or ride the elevator up to Z Bar above the Peninsula Hotel.
If you want the ultimate skyscraper view, grab a drink at LondonHouse, which sits right on the curve of the Chicago River.
You get the exact same sweeping, jaw-dropping views of the skyline and the water, but you get to enjoy it while sipping a martini in a plush leather chair.
10. Underestimating the Wind Off the Lake
You check the weather app in the morning, see that it’s 65 degrees, and head out the door in a t-shirt.
Two hours later, you are standing near Lake Michigan, shivering uncontrollably.
Tourists constantly underestimate the micro-climate created by the lake.
What To Do Instead:
We aren’t called the “Windy City” for nothing (even if that nickname originally came from our boastful politicians, not the weather!).
The breeze coming off of Lake Michigan can easily drop the temperature by 10 to 15 degrees the closer you get to the water.
Always pack layers, and never leave your hotel without a light jacket or sweater, even if it looks perfectly sunny outside.
11. Wasting a Whole Day at Navy Pier
Navy Pier is the number one tourist attraction in the Midwest, so naturally, most visitors plan to spend an entire afternoon there.
While the Ferris wheel looks great in photos, the actual pier is essentially just a giant, crowded outdoor mall.
Unless you are going to the Shakespeare Theater or have small children who want to visit the Children’s Museum, it is largely considered a massive, overpriced tourist trap by locals.
What To Do Instead:
Skip the crowded pier and head to the Chicago Riverwalk instead.
It is a stunning, pedestrian-only path right on the water that winds through the towering canyons of downtown architecture.
It is packed with great outdoor wine bars, public art, and much better views of the city’s iconic buildings.
